6-Chloro-3-formyl-2-picoline

To a 3 L 3-neck flask was added EtTo a 3 L 3-neck flask was added Etl-methyl-6-oxo-l, 6-dihydropyridine-3-carbaldehyde: To a solution of 6- chloro-2-methylnicotinaldehyde (1.0 g, 6.43 mmol) in cone. HC1 (3 mL), was heated to 90 C for O.N. Cooled it down and poured it to ice water (20 mL). Filtered and dried with vacuum. Used without further purification. To a suspension of 6-oxo-l, 6-dihydropyridine-3-carbaldehyde (300 mg, 2.19 mmol) in DMF, sodium hydride (96 mg, 2.4 mmol) was added to the suspension under ice bath condition. lodomethane (0.15 mL, 2.4 mmol) was added to the suspension. Then it was stirred for overnight. Diluted with EtOAc and washed with brine. The organic layer was dried and concentrated. Used without further purification.Step 2: A mixture of compound 8-2 (0.55 g, 3.5 mmol), NaBH4 (0.4 g, 10.5 mmol) in dry THF (40 mL) was stirred at rt for 6 hours. After quenched with H20 (30 mL), the mixture was extracted with EtOAc (30 mL x 2). The combined organic layer was dried over Na2S04 and concentrated. The resulting residue was purified by column chromatography to give product 8-3 as yellow oil. LC-MS: m/z = 158.0 [M+H]+.

Molecular Weight:155.58
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:155.0137915
Monoisotopic Mass:155.0137915
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes